Hydroxyamine hydrochloride → N-{1-[(4-chlorophenyl)methyl]piperidin-4-ylidene}hydroxylamine

HRID 1017325Notes

Reaction equation

HRID 1017325 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][C:10](=[N:17][OH:18])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 105610671-[(4-Chlorophenyl)methyl]piperidin-4-one

Product 1

HCID 12641825N-{1-[(4-chlorophenyl)methyl]piperidin-4-ylidene}hydroxylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 1-(4-chlorobenzyl)-4-piperidone (0.0456 mmol), hydroxylamine hydrochloride (0.0456 mmol) and sodium acetate (0.0456 mmol) in aqueous ethanol (450 mL). Stir approximately 30 minutes to 2 hours while warming. Add methylene chloride (450 mL), separate the organic phase, and extract the aqueous phase with methylene chloride (100 mL). Combine the organic phases and dry (MgSO4). Evaporate the solvent in vacuo to give the title compound.

Workup

  1. temperaturewhile warming
  2. customAdd methylene chloride (450 mL), separate the organic phase
  3. extractionextract the aqueous phase with methylene chloride (100 mL)
  4. dry with materialCombine the organic phases and dry (MgSO4)
  5. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-4b68bd0f38fd491b89528e45c1460325
Source dataset
uspto-grants-2002_11
Patent number
US06479487B1

Reaction notes

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